3-{2,4-Dimethyl-5-[(2-oxo-6-phenyl-1,2-dihydro-3H-indol-3-ylidene)methyl]-1H-pyrrol-3-yl}propanoic acid

Base Information

• Chemical Name: 3-{2,4-Dimethyl-5-[(2-oxo-6-phenyl-1,2-dihydro-3H-indol-3-ylidene)methyl]-1H-pyrrol-3-yl}propanoic acid
• CAS No.: 251356-45-3
• Molecular Formula: C₂₄H₂₂N₂O₃
• Molecular Weight: 386.45
• DSSTox Substance ID: DTXSID90694250
• Mol file: 251356-45-3.mol

Synonyms:SU16f;SCHEMBL4408686;DTXSID90694250;APYYTEJNOZQZNA-UHFFFAOYSA-N;3-[2,4-Dimethyl-5-(2-oxo-6-phenyl-1,2-dihydroindol-3-ylidenemethyl)-1H-pyrrol-3-yl]-propionic acid;3-{2,4-Dimethyl-5-[(2-oxo-6-phenyl-1,2-dihydro-3H-indol-3-ylidene)methyl]-1H-pyrrol-3-yl}propanoic acid

Chemical Property of 3-{2,4-Dimethyl-5-[(2-oxo-6-phenyl-1,2-dihydro-3H-indol-3-ylidene)methyl]-1H-pyrrol-3-yl}propanoic acid

Chemical Property:

• Boiling Point: 661.7±55.0 °C(Predicted)
• PKA: 4?+-.0.10(Predicted)
• PSA: 82.19000
• Density: 1.292±0.06 g/cm3(Predicted)
• LogP: 4.94640
• Storage Temp.: Store at RT
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 386.16304257
• Heavy Atom Count: 29
• Complexity: 655

Purity/Quality:

≥98% by HPLC ^*data from raw suppliers

SU 16f ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(NC(=C1CCC(=O)O)C)C=C2C3=C(C=C(C=C3)C4=CC=CC=C4)NC2=O
• Uses: SU 16f is used in the synthetic preparation of [(Dihydrooxoindolylidene)methyl]pyrrolepropanoic Acid as a tyrosine kinase inhibitor.

Technology Process of 3-{2,4-Dimethyl-5-[(2-oxo-6-phenyl-1,2-dihydro-3H-indol-3-ylidene)methyl]-1H-pyrrol-3-yl}propanoic acid

There total 14 articles about 3-{2,4-Dimethyl-5-[(2-oxo-6-phenyl-1,2-dihydro-3H-indol-3-ylidene)methyl]-1H-pyrrol-3-yl}propanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

2-nitro-4-phenylbenzeneacetic acid (80726-56-3) → 6-phenyl-2-oxindole (90751-00-1) + SU 16f (251356-45-3)

Guidance literature:

In acetic acid; ethyl acetate;

Reference yield: 71.0%

3-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)-propionic acid (1133-96-6) + 6-phenyl-2-oxindole (90751-00-1) → SU 16f (251356-45-3)

Guidance literature:

With piperidine; In ethanol; at 95 ℃; for 5h;

DOI:10.1021/jm9904295

Reference yield:

benzyl 4-(2-methoxycarbonylethyl)-3,5-dimethylpyrrole-2-carboxylate (20303-31-5) → SU 16f (251356-45-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / H₂ / 10 percent Pd/C / methanol / 2 h / 20 °C

2: 38 percent / NaOAc / methanol / 72 h / 100 °C

3: 60 percent / 1,2-dichloro-ethane / 2 h / 20 °C

4: 6 N aq. NaOH / 2 h / 100 °C

5: 71 percent / piperidine / ethanol / 5 h / 95 °C

With piperidine; sodium hydroxide; hydrogen; sodium acetate; palladium on activated charcoal; In methanol; ethanol; 1,2-dichloro-ethane; 1: Hydrogenolysis / 2: Decarboxylation / 3: Formylation / 4: Hydrolysis / 5: Condensation;

DOI:10.1021/jm9904295

upstream raw materials:

3-(5-formyl-2,4-dimethyl-1H-pyrrol-3-yl)-propionic acid

6-phenyl-2-oxindole

2-nitro-4-phenylbenzeneacetic acid

4-Bromo-1-fluoro-2-nitrobenzene

Refernces

• 1、 -. "Pyrrole substituted 2-indolinone protein kinase inhibitors". . . Retrieved 2008/06/13.